Rentboy – Largest Gay Male Escort and Massage Site

Advanced Search

filters



Sexual Position




Cock



Rates


Ethnicity











Interests




















Body Hair






Build








Safe Sex





89 male escorts and male massage therapists In Chicago, Illinois

card grid realtime
page of 5

Sorry!

The ad you tried to reach is no longer available. Below are ads in the same location as the ad you tried to reach... or try searching again.

Actively Looking
- Versatile Cut

Military Beefy Hairy Charming Educated Sweet Stud

Professional muscle bodybuilder great personality, mild to wild escort or sensual massages.  I enjoy all types of places food music available for travel  I am lucky to meet great guys from this site. I have a big sweet smile charming kind heart traveled intelligent up for intimacy romantic... (more)
Click to open map Chicago, IL
My Phone Number
+1 (646) 807-9356
Email
In Rate Out Rate
$200 $280

For Those Whom Appreciate Customer Satasfaction

  First and formost I would like to thank the 3.5 million viewers for ranking my performance one of the all time highest rated & most watched in pornhuBB history. Never saw that coming. That said, if you know what you like and like what you see...then indulge yourself. SXVideo porn talent, ... (more)
I'm #2 on the map Chicago, IL
My Phone Number
+1 (773) 642-6402
Email
In Rate Out Rate
Ask me $250.00

Furball visiting 8/4-8/10

Exploring your sexuality is as exciting as it is scary. I'm a handsome, furry, built, and educated guy who is always excited to show you around and share my experiences. Very discreet, easy-going and down-to-earth. Passionate, tactile, love to kiss and a cuddler at heart with a kinky side. I am... (more)
Chicago, IL
My Phone Number
+1 (206) 432-0042
Email
In Rate Out Rate
$220 $250

Hung, passionate and focused on complete satisfaction.

All American, Masculine, THICK DICK TOP-    Discrete, clean and confident guy, well traveled and well read who can hold a decent conversation!   Always horny, not so inocent in bed and very experienced in pleasure. Relax I am very respectful and have zero attitude! &nbs... (more)
I'm #3 on the map travel adChicago, IL
My Phone Number
+1 (415) 548-0511
Email
In Rate Out Rate
NA $250

FOR SALE BY OWNER.

Hey there, my name is Kapov , 40 years , 6'0", HIV neg ( ON PREP ), my dick is 8 inches(not less). I live in  E LAKE VIEW - CHICAGO where I can have you in my private apt. Your pleasure is my pleasure and my goal. Always assertive, passionate and TOP / Versatile. I'm open to most scenes , let m... (more)
I'm #4 on the map Chicago, IL
My Phone Number
+1 (773) 891-8532
Email
In Rate Out Rate
$250.00 CREDIT CARD OR CASH $270.00 CREDIT CARD OR CASH

Actively Looking
26 Versatile Cut

IN CHI NOW - AUG 5TH 614-648-0966

Just a good old mid-western boy here. I'm 25 5'10 175lbs blonde hair, clean cut, blue eyes, 7" cut with nice bubble butt, naturally smooth. Workout 5 days a week now, stay healthy and tan. I enjoy being a top and bottom but really like to pile drive when I top. Open to most scenes with only a few li... (more)
Chicago, IL
My Phone Number
+1 (614) 648-0966
Email
In Rate Out Rate
$250 $250

The Best Top In Chicago 310-927-9484

  I always deliver, never under perform.I can be your passionate boyfriend or a dominant and aggressive pig.  i get into most every scene, if you have any questions feel free to ask. I absolutely enjoy what i do and i'm good at it.  i'm well reviewed, i dont play games or watch ... (more)
Chicago, IL
My Phone Number
+1 (310) 927-9484
Email
In Rate Out Rate
Ask me $250

All American Blond Boy next door!

Hello!  ;) I am a good looking, educated, funny, masculine guy. I am really easy to get along with and always try to live in the moment.  I have my dirty, goofy/corkey side, my serious intellectual side, my creative artsy/musical side, my passionate caring side & my wild side!  :... (more)
Chicago, IL
My Phone Number
+1 (954) 901-5282
Email
In Rate Out Rate
$200 $250

Toned Pre-med Student

Hi guys! I am an easy-going fit student, new to Chicago, who enjoys meeting nice guys of any age. I have a lean, athletic build and I enjoy working out, martial arts, and reading. I don't meet a lot of guys, which keeps things relaxed and fun, and tend toward more vanilla activities. You can be... (more)
Chicago, IL
My Phone Number
+1 (773) 418-2921
Email
In Rate Out Rate
n/a $240

I'm a graduate student in Chicago looking to make a few new connections.   Treat me with respect and I'll do the same for you. I cannot answer calls from blocked or private numbers.   Like to know more? Don't hesitate to contact me. I'm pretty friendly, and I make every effort to respo... (more)
Chicago, IL
My Phone Number
+1 (312) 972-9793
Email
In Rate Out Rate
Ask me $200

In Chicago til Aug 5! Return Aug 21!

I'm a hot and passionate companion. I can get into intelligent conversation over a nice dinner as easily as I get into sensual play. You will find that I am dependable, professional, real and easy to get along with. I enjoy theatre, travel, fine dining, shopping, movies, and more.  I returned t... (more)
I'm #5 on the map Chicago, IL
My Phone Number
+1 (773) 870-2154
Email
In Rate Out Rate
$225/hr $250/hr

Southern boy-next-door

  Laid back, confident, very good looking. Boy next door type. Over all great guy. Gym 5x a week. Southern born and raised, accent and all. I genuinely enjoy what I do, so I have no doubt you'll enjoy what I do too. I respect everyone's privacy and any encounter is between us. Feel free to con... (more)
I'm #6 on the map Chicago, IL
My Phone Number
+1 (404) 860-1213
Email
In Rate Out Rate
$225 $250

Chicago Aug 4-10

Easy going and educated young jock. I enjoy working out, going to the theatre, and midnight movies. Earned my degree studying media regulation and further pursuing a carrer in that field. I also have performed in porn, with scenes ranging from vanilla to kink. I can rock a pair of leather pants an... (more)
travel adChicago, IL
My Phone Number
+1 415-347-1853
Email
In Rate Out Rate
Ask me Ask me

Vers Corn-Fed Beef!

  Companionship and conversation are a no brainer for me - whether its cocktails and dinner you'd like, you just need some man to man time with the boyfriend experience or my magic hands if you so desire, I do give a damn good massage. I am mild to wild kinky or vanilla and very well experien... (more)
Chicago, IL
My Phone Number
+1 (402) 871-6928
Email
In Rate Out Rate
$200 $240

Established Male Geisha: mild 2 wild

SF: 6/16-17 & 28th-7/2... Seattle & Portland 7/3-18th. Possible travel to NYC, DC, MN and IN during that time at the beginning of July or end of if and early august~ U.S. / international companion w/ excellent reviews~ (15 yrs experience). Responsible, stable, dependable. Happy go lucky/horn... (more)
Chicago, IL
My Phone Number
+1 (971) 400-2633
Email
In Rate Out Rate
$2hrs=$350, 3hrs=$500, 6hrs=$600 $2hrs=$350, 3hrs=$500, 6hr=$600

Lets have fun

Hello, thank you for checking out my ad. My name is Ron, I'm 18 years old And just started college. I'm very athletic, I enjoy exercising and staying in shape. Took ballet for 3 year along with karate for 4. I'm Very talented and intelligent. I enjoyianything and like to try new things; very open mi... (more)
Chicago, IL
My Phone Number
+1 (630) 624-8775
Email
In Rate Out Rate
N/A $200

Furry Young Man

Hi, I'm Clark! Back in Chicago Young, sensual, and all man. Totally versatile and looking to have some fun with you! Fluent in three languages and friendly in all of them.   I respect your requirement for discretion while I tend to your more intimate needs. Professional, intelligent, sexy, a... (more)
Chicago, IL
My Phone Number
+1 (312) 401-7393
Email
In Rate Out Rate
$250 $250

11x8 ....ONE OF THE BIGGEST. IN CHICAGO FOR 5 DAYS ONLY. AVAILABLE !

Very hot and muscled TOP. Very well hung and very thick.   A REAL 11x8, Very attractive, smooth skin toned guy here.. Available.. Also I can travel locally and internationally. Masculine and mature here .  o call or text me. No private calls accepted. 414-736-2297 Wesley
I'm #7 on the map travel adChicago, IL
My Phone Number
+1 (414) 736-2297
Email
In Rate Out Rate
$300 $300

Actively Looking
30 Versatile Cut

Dtn Boy Next Door type: I'm a dork, and its ok to laugh at that

My profile may seem different from others on here and well, that's because I am. Im not gonna talk about my raging hard cock, or how much I can benchpress. I like getting dressed up to look sharp when meeting a client, it makes me feel confident about myself and you're spending your hard earned... (more)
Click to open map Chicago, IL
My Phone Number
+1 719-924-7040
Email
In Rate Out Rate
$200 $200

Boy-Next-Door Gives Stimulating & Exciting Encounters

All-American Jock; Holder of Undergraduate & Master's diplomas; Apprentice of Elite Acting & Teaching programs; AND most importantly...a BLAST in the BEDROOM.Rough-N-Tumble kind of guy who is also an excellent Active Listener with amazing Empathy. You will experience me to be Sweet, Engaging... (more)
Chicago, IL
My Phone Number
+1 (760) 898-0613
Email
In Rate Out Rate
(only at Steamwoks) $200

Actively Looking
24 Versatile Cut

The Charmer - (317) 762-5728

Howdy boys! I am fairly new to this city and would love some good company.  Just moved here a couple weeks ago and trying to get on my feet here.  I am a strong, masculine vers guy with an extensive athletic background. I love to dance, and I love cuddling.  I have an extremely easy-g... (more)
travel adChicago, IL
My Phone Number
+1 (317) 762-5728
Email
In Rate Out Rate
$200 $220

DaddyCub duJour

Not your average DaddyCub. Im your above average, versatile musclecub with meat on his bones and a bone in his jock.  Young. Gregarious. Frisky. Into a more kinkier side. Im open minded about many fetishes and have experience in various aspects of kink and fetishes in part of my day job. That ... (more)
Chicago, IL
My Phone Number
+1 (978) 325-1890
Email
In Rate Out Rate
$200.00 $200.00

page of 5
in/out rate
in rateIn Rate
out rateOut Rate
star rating
rate from 1 to 5rate from 1 to 5
unratedunrated
Foreskin
cutCut
uncutUncut
Age
# of years# of years
Sexual Position
topTop
bottomBottom
versatileVersatile

signup for the rentboy.com newsletter

Don’t miss out on our latest news, events, and the sexiest men available near you!